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Degradation reference materials 2017N-oxides

Certificate of Analysis — ExampleWelcome to LGCs degradation reference standards with focus on N-oxides.

Active pharmaceutical ingredients (APIs) containing nitrogen as an amine are prone to degrade to N-Oxides readily and quickly under oxidative stress.

LGC’s impurity reference standards are designed to be used at all relevant stages of the testing chain. The use of our N-Oxide impurities facilitate an assessment of the oxidative stress a particular product has been subjected to, the purity of the originating API, and help determine the shelf life of the product.

Each impurity is accompanied by a detailed certificate of analysis, providing all the information you need to best use the reference material. Our products can be used with confidence during analytical research and development and validation studies as well as for stability monitoring and routine quality control purposes.

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To find out more contact your local LGC office.

LGC provides a range of N-oxide impurity reference standards for more than 180 major APIs.

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Certificate of Analysis — Example

LGC GmbH, Im Biotechnologiepark, TGZ II, D-14943 Luckenwalde, Germany 6 Pages

Certificate of Analysis

Catalogue Number: MM0095.16

Lot Number: 119760

Long-term Storage: 2 to 8 °C, dark

Appearance: white solid

Melting Point: 185 °C (dec.)

Assay ʻas isʼ: 99.6 %

Reference Standard

4-Methoxy-2-[[(5-methoxy-1H-benzimidazol-2-yl)sulphonyl]methyl]-3,5-dimethylpyridine 1-Oxide (Omeprazole Sulphone N-Oxide)

Molecular Formula: C17H19N3O5S Molecular Weight: 377.42 CAS Number: 158812-85-2

Date of shipment: 2017-June-30

This certificate is valid for two years from the date of shipment provided the substance is stored under the recommended conditions unopened in the original container.


MM0095.16 lot number 119760 LGC GmbH, Im Biotechnologiepark, TGZ II, D-14943 Luckenwalde, Germany

Page 2/6

I. Identity

The identity of the reference substance was established by following analyses.

Ia. 1H-NMR Spectrum

Conditions: 400 MHz, DMSO-d6

The structure is confirmed by the signals of the spectrum and their interpretation.



Page 3/6

Ib. Mass Spectrum

Method: 3.5 kV ESI+; capillary temperature: 269 °C

Theoretical value: 378.11182

The signal of the MS spectrum is consistent with the theoretical value and its interpretation is consistent with the structural formula.



Page 4/6

Ic. IR Spectrum

Method: Attenuated Total Reflection Fourier Transform Infrared (ATR-FTIR) Spectroscopy

The signals of the IR spectrum and their interpretation are consistent with the structural formula.

II. Purity

IIa. High Performance Liquid Chromatography (HPLC)

The purity of the reference substance was analysed by high performance liquid chromatography (HPLC).

HPLC Conditions: Column: Conditions: Detector: Injector:

Hypersil Gold C18 1.0 ml/min, 40 °C DAD Auto 5 µm, 150 x 4.6 mm 0-15 min Water/Acetonitrile 80/20

15-20 min Water/Acetonitrile to 60/40 20-25 min Water/Acetonitrile 60/40 25-30 min Water/Acetonitrile to 80/20 30-35 min Water/Acetonitrile 80/20 (v/v); 0.1 % H3PO4

220 nm 5 µl; 0.0696 mg/ml in Water/Acetonitrile 50/50 (v/v)



Page 5/6

Area Percent Report - Sorted by Signal

Pk # Retention Time Area Area %1 5.867 0.042 0.03 2 9.083 132.108 99.97

Totals 132.149 100.00

For the calculation the system peaks were ignored. The content of the analyte was determined as ratio of the peak area of the analyte and the cumulative areas of the purities, added up to 100 %.

Results: Average 99.97 % Number of results n=3 Standard deviation < 0.01 %

IIb. Water Content

Method: Karl Fischer titration

Results: Average 0.22 % Number of results n=3 Standard deviation 0.01 %



Page 6/6

IIc. Residual Solvents

Method: 1H-NMR

Result: 0.06 % Acetic acid 0.03 % Dichloromethane 0.02 % n-Hexane

III. Final Result

Chromatographic purity (HPLC) 99.97 % Water content 0.22 % Residual solvents 0.11 % Assay (100 % method)1 99.64 %

The assay is assessed to be 99.6 % ʻas isʼ

The assay 'as is' is equivalent to the assay based on the not anhydrous and not dried substance respectively.

Release Date: Luckenwalde, 2016-12-13

Dr. Sabine Schröder Product Release

1 The calculation of the 100 % method follows the formula:

Assay (%) = (100 % - volatile contents) Purity (%)100 %*

Volatile contents are considered as absolute contributions, purity is considered as relative contribution.

Products — N-oxides

A–Z of productsN-oxidesA. Amiodarone Hydrochloride — Azaperone

B. Bamifylline Hydrochloride — Butorphanol Tartrate

C. Carbinoxamine Maleate — Cyproheptadine Hydrochloride

D. Deanol Acetamidobenzoate — Droperidol

E. Ebastine — Escitalopram Oxalate

F. Fentanyl — Furaltadone

G.Gefitinib — Granisetron Hydrochloride

H. Halofantrine Hydrochloride — Hyoscyamine Sulfate

I. Imipramine Hydrochloride

K. Ketoconazole — Ketotifen Hydrogen Fumarate

L. Lansoprazole — Loxapine Succinate

M. Mebhydrolin Napadisilate — Mycophenolate Mofeti

N. Nalbuphine Hydrochloride — Nikethamide

O. Ofloxacin — Oxycodone Hydrochloride

P. Pantoprazole Sodium Sesquihydrate — Proxymetacaine Hydrochloride

Q. Quetiapine Fumarate — Quinine Hydrochloride

R. Rabeprazole Sodium — Rotigotine Hydrochloride

S. Sildenafil Citrate — Sumatriptan Succinate

T. Tamoxifen Citrate — Tropicamide

V. Vardenafil Hydrochloride Trihydrate — Vinpocetine

X.Xanthinol Nicotinate

Z. Zolmitriptan — Zopiclone

Products — N-oxidesDegradation products - N-Oxides

CAS No. CS UnitProductCode

Amiodarone Hydrochloride

MM0697.10 Amiodarone N-Oxide Hydrochloride n/a 100mg HClI

ON

+ O

I

O

O

Amitriptyline Hydrochloride

MM0062.12 Amitriptyline N-Oxide Hydrochloride 4290-60-2 10mg HClN+

O

Amodiaquine Dihydrochloride Dihydrate

MM0617.08 Amodiaquine N-Oxide 102391-07-1 100mg

N

NH

N+

O

OH

Cl

Aripiprazole

MM0961.03 Imp. F (EP): 7-[4-[4-(2,3-Dichlorophenyl)-1-oxidopiperazin-1-yl]butoxy]-3,4-dihydroquinolin-2(1H)-one (Aripiprazole N-Oxide) 573691-09-5 100mg

O

N+

N

Cl

Cl

O NH

O

Atropine

MM0289.19 Atropine N-Oxide Hydrochloride 4574-60-1 100mg ON

+

H

O

H

HO

OH

HCl

AND Enantiomer

Azaperone

MM1164.01 Azaperone N-Oxide 66065-28-9 100mgN

N

N+

F

O

O

Bamifylline Hydrochloride

MM1823.01 Bamifylline N-Oxide n/a 100mg N

O

N

N+

OH

O

NNO

Benactyzine Hydrochloride

MM1826.02 Benactyzine N-Oxide 42771-70-0 100mgOH O

ON

+O

Benperidol

MM0113.09 Mixture of Imp. D and E (EP): Benperidol N-Oxide (cis andtrans) 118435-01-1 25mg

F

O

N+

O

N

NHO

Benztropine Mesilate

MM1227.02 Benztropine N-Oxide Hydrochloride n/a 100mg N +O

H

H

H

O

HCl

A-1Edition 2017 Visit us at www.lgcstandards.com



Benzydamine Hydrochloride

MM0142.08 Benzydamine N-Oxide Hydrochloride 39860-94-1 100mg HClN

N

O N+

O

Biperiden Hydrochloride

MM0288.07 Biperiden N-Oxide n/a 100mg N +OOHHH

H

AND Enantiomer

MM0288.08 Biperiden Epoxide N-Oxide n/a 100mg N +OOHH

O

H

H

AND Enantiomer

Bromhexine Hydrochloride

MM0065.09 Bromhexine N-Oxide n/a 100mg

Br

N+

ON H 2

Br

Brompheniramine Maleate

MM0060.12 Brompheniramine N-Oxide 18453-29-7 100mgN

Br

N+

O

Buflomedil Hydrochloride

MM0066.12 Buflomedil N-Oxide Hydrochloride n/a 100mg HCl

O

N+

OO

OO

Bupivacaine Hydrochloride

MM0613.07 Bupivacaine N-Oxide n/a 100mg NH

N+

OO

Buprenorphine

MM0120.15 Buprenorphine N-Oxide 112242-17-8 100mgH

OH

OOH O

N+O

Buspirone Hydrochloride

MM0464.18 Buspirone N-Oxide 220747-81-9 100mg N

O

N+

N

N

N

O

O

Butacaine Sulfate

MM1638.01 Butacaine N-Oxide n/a 100mg N+

O

O

NH 2

O




MM1638.02 Butacaine N-Oxide Hydrochloride n/a 100mg HClO

N+

O

NH 2

O

Butalamine Hydrochloride

MM1845.02 Butalamine N-Oxide n/a 100mg N

ON

NH

N+

O

Butorphanol Tartrate

MM1192.01 Butorphanol N-Oxide 112269-63-3 100mg

OH

OH

N+O

Carbinoxamine Maleate

MM1135.01 Carbinoxamine N-Oxide 1256285-70-7 100mg N+O

Cl

NO

Cetirizine Dihydrochloride

MM0380.13 Cetirizine N-Oxide 1076199-80-8 100mgCl

N

N+ O

OH

OO

Chlorcyclizine Hydrochloride

MM1653.01 Chlorcyclizine N-Oxide 10457-56-4 100mg

Cl

N

N+

O

Chloropyramine Hydrochloride

MM1894.02 Chloropyramine N-Oxide n/a 100mgN

+N

Cl

N

O

Chlorphenamine Maleate

MM0090.11 Chlorphenamine N-Oxide Dihydrochloride n/a 100mg2

HCl

Cl

NN

+

O

MM0090.15 Chlorphenamine N-Oxide Maleate n/a 100mgO

OH

O

OH

Cl

NN

+

O

Chlorphenoxamine Hydrochloride

MM1291.02 Chlorphenoxamine N-Oxide 110203-91-3 100mgCl

ON

+O




Chlorpromazine Hydrochloride

MM0420.02 Chlorpromazine Sulphoxide N-Oxide Maleate 150111-59-4 10mgO

OH

O

OHN

SO

N+

O

Cl

MM0420.11 Chlorpromazine Sulfone N-Oxide Hydrochloride(Chlorpromazine N,S,S-Trioxide Hydrochloride) 109724-46-1 100mg HCl

Cl

N N+

OSOO

MM0420.13 Chlorpromazine N-Oxide Hydrochloride n/a 100mg HCl

Cl

N N+

OS

Cinchocaine Hydrochloride

MM0604.05 Cinchocaine N-Oxide 87864-07-1 100mg N

NH

N+

O

O

O

Citalopram Hydrobromide

MM0242.10 Citalopram N-Oxide 63284-72-0 100mg

F

N+

OO

N

Clindamycin Phosphate

MM1520.05 Clindamycin Phosphate Sulfone trans-N-Oxide n/a 100mgCl

O

N+

O

NH

S

O O

PO

OHOH

OOH

OOH

Clomifene Citrate

MM0650.01 Clomifene N-Oxide Hydrochloride 97986-33-9 100mgHCl

Cl

ON

+

O

Clomipramine Hydrochloride

MM0545.09 Clomipramine N-Oxide 14171-67-6 100mg N+

ON

Cl

Clozapine

MM0480.07 Clozapine N-Oxide 34233-69-7 100mgN

N+

ON

NH

Cl

Codeine

MM0004.01 Codeine N-Oxide 3688-65-1 CS 250mg H

N +O

O O HO




Cyclizine Hydrochloride

MM1265.04 Cyclizine N-Oxide Dihydrochloride n/a 100mg2

HClN

N+

O

Cyclobenzaprine Hydrochloride

MM1248.03 Cyclobenzaprine N-Oxide Hydrochloride n/a 100mg HClO

N+

Cyclopentolate Hydrochloride

MM0580.05 Cyclopentolate N-Oxide Hydrochloride n/a 100mg HCl

O

ON

+O

OH

Cyproheptadine Hydrochloride

MM0609.05 Cyproheptadine -N-Oxide 54381-42-9 100mgN

+

O

alpha-Isomer

MM0609.06 Cyproheptadine -N-Oxide 60251-34-5 100mgN

+

O

beta-Isomer

Deanol Acetamidobenzoate

MM1681.01 Deanol N-Oxide 10489-99-3 100mgOH

N+

O

Dexchlorpheniramine Maleate

MM1114.03 Dexchlorpheniramine N-Oxide Dihydrochloride n/a 100mgN

N+

O

Cl

2HCl

Dextromethorphan Hydrobromide

MM0033.11 Dextromethorphan N-Oxide Hydrochloride 1177419-85-0 100mg H

N+

O

O

HCl

Diethazine Hydrochloride

MM1593.08 Diethazine N-Oxide Hydrochloride n/a 100mgHCl

O

N+

N

S

MM1593.09 Diethazine Sulfoxide N-Oxide Hydrochloride (Diethazine N,S-Dioxide Hydrochloride) n/a 100mg

HClO

N+

N

SO

MM1593.10 Diethazine Sulfone N-Oxide Hydrochloride (Diethazine N,S,S-Trioxide Hydrochloride) n/a 100mg

HClO

N+

N

SOO




Difenidol Hydrochloride

MM3053.01 Difenidol N-Oxide 40220-79-9 100mg OHN

+O

Dihydrocodeine Hydrogen Tartrate

MM0812.08 Dihydrocodeine N-Oxide 109667-32-5 100mgN

+O

OO O H

H

Dimetindene Maleate

MM0595.13 Dimetindene N-Oxide Dihydrochloride n/a 100mg 2HCl

N

N+

O

Diphenhydramine Hydrochloride

MM0490.01 Diphenhydramine N-Oxide 3922-74-5 100mgO

N+ O

Diphenylpyraline Hydrochloride

MM0557.04 Diphenylpyraline N-Oxide 10020-59-4 100mgO

N+

O

Disopyramide

MM0108.09 Disopyramide N-Oxide Dihydrochloride n/a 100mg2

HCl

O

N+

N

N H 2

O

Donepezil Hydrochloride

MM0677.14 Donepezil N-Oxide 120013-84-5 50mgN

+O

O

O

O

Dosulepin Hydrochloride

MM0510.13 Dosulepin Sulfoxide N-Oxide Hydrochloride (Dosulepin N,S-Dioxide Hydrochloride) n/a 100mg

HCl

ON

+

SO

MM0510.14 Dosulepin Sulfone N-Oxide Hydrochloride (Dosulepin N,S,S-Trioxide Hydrochloride) n/a 100mg

HCl

ON

+

SO O




Doxapram Hydrochloride

MM0525.03 Doxapram N-Oxide n/a 100mgN O

N+

O

O

Doxepin Hydrochloride

MM0032.12 Doxepin N-Oxide Hydrochloride n/a 100mg HCl

O

N+

O

Doxylamine Hydrogen Succinate

MM0101.05 Doxylamine N-Oxide Dihydrochloride n/a 100mg 2HClN

ON

+ O

Drofenine Hydrochloride

MM0768.01 Drofenine N-Oxide Hydrochloride n/a 100mg HClO

N+

OO

Droperidol

MM0138.04Imp. D (EP) as Hydrochloride: (1RS)-1-[4-(4-Fluorophenyl)-4-oxobutyl]-4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1,2,3,6-tetrahydropyridine 1-Oxide Hydrochloride

n/a 100mg HClN

+

N

NHO

F

O

O

Ebastine

MM0468.09 Mixture of Imp. F and G (EP): Ebastine N-Oxide (cis andtrans) 1256285-71-8 50mg

O

N+

O

O

Emedastine Difumarate

MM1277.09 Emedastine N-Oxide Difumarate n/a 100mg2

O

OHOH

ON

N

N

N+

OO

Enrofloxacin

MM0395.07 Enrofloxacin N-Oxide Hydrochloride n/a 100mg HClN

O

OH

O

F

N

N+

O

Escitalopram Oxalate

MM1162.05 Escitalopram N-Oxide 917482-45-2 100mg

F

N+

OO

N




Fentanyl

MM0528.09Imp. A (EP) as Hydrochloride: N-Phenyl-N-[cis,trans-1-oxido-1-(2-phenylethyl)piperidin-4-yl]propanamide Hydrochloride (FentanylN-Oxide Hydrochloride)

n/a 100mg HCl

N+

O

N

O

Fexofenadine Hydrochloride

MM0507.10 Fexofenadine N-Oxide 1422515-52-3 25mg OH

N+

O

OH

O

OH

Flavoxate Hydrochloride

MM0156.07 Flavoxate N-Oxide Hydrochloride n/a 100mg HCl

O ON

+

O

O

O

Flunarizine Dihydrochloride

MM0175.06 Flunarizine N-Oxide Dihydrochloride n/a 100mg 2HCl

N

F

F

N+

O

Flupentixol Dihydrochloride

MM0223.14 Flupentixol N1-Oxide Dihydrochloride n/a 50mg2

HCl

FF

S

N

N+

OOH

F

Fluphenazine Dihydrochloride

MM0114.04 Fluphenazine N,N',S-Trioxide Dihydrochloride n/a 100mg2

HClS

N N+

N+

OHO

O

F

F F

O

MM0114.15 Fluphenazine N1-Oxide Dihydrochloride n/a 100mg 2HCl

FF

F

N N

N+

OOH

S

MM0114.18 Fluphenazine Sulfone N1,N4-Dioxide (FluphenazineN1,N4,S,S-Tetraoxide) 86137-45-3 100mg O

SO

FF

F

N N+

O

N+

OOH

Furaltadone

MM1753.02 Furaltadone N-Oxide Hydrochloride n/a 100mg HCl

ON

+O

ON

N

ON+

O

O

O

Gefitinib

MM3563.01 Gefitinib N-Oxide 847949-51-3 100mg N+

O

ON

N

NH

F

Cl

O

O

Granisetron Hydrochloride

MM0398.11 Granisetron N-Oxide 160177-68-4 50mg N+

NH

O

NNH

O

H




Halofantrine Hydrochloride

MM0433.05 Halofantrine N-Oxide 1348409-88-0 100mg F

F F

Cl

Cl

N+

OOH

Homatropine Hydrobromide

MM1649.02 Homatropine N-Oxide Hydrochloride n/a 100mgO H

O

O

H

H

H

N +O HCl

AND Enantiomer

Hydrocodone Hydrogen Tartrate 2.5-Hydrate

MM1113.17 Hydrocodone N-Oxide 909265-05-0 100mg

O O

H

N+O

O

Hydromorphone Hydrochloride

MM0371.09Imp. B (EP) as Hydrochloride: 4,5 -Epoxy-3-hydroxy-17-methylmorphinan-6-one 17-Oxide Hydrochloride(Hydromorphone N-Oxide Hydrochloride)

n/a 100mg H

OO

N+O

OH

HCl

Hydroxychloroquine Sulphate

MM0764.05 Hydroxychloroquine N-Oxide Dihydrochloride n/a 10mg 2HCl

N

NHN

+ OH

O

Cl

Hyoscine Hydrobromide

MM0546.07 Hyoscine N-Oxide Hydrobromide 6106-81-6 100mg N+

O

H

HO

H

H

OH

OH

OHBr

Hyoscyamine Sulfate

MM0794.09 Hyoscyamine N-Oxide Hydrochloride 200721-88-6 100mgOH

OH

H

N+O

H

OHCl

Imipramine Hydrochloride

MM0077.12 Imipramine N-Oxide 6829-98-7 100mg N+

ON

Ketoconazole

MM0145.07 Ketoconazole N-Oxide 254912-65-7 100mgN

+O

O

N

N

Cl Cl

OO

NO

AND Enantiomer




Ketotifen Hydrogen Fumarate

MM0180.07Imp. D (EP): 4-[(aRaS)-1-Methylpiperidin-4-ylidene]-4,9-dihydro-10H-benzo[4,5]cyclo-hepta[1,2-b]thiophen-10-one N-Oxide(Ketotifen N-Oxide)

88456-70-6 100mgS

O

N+

O

Lansoprazole

MM0474.07Imp. A (EP): 2-[(RS)-[[3-Methyl-1-oxido-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]-sulphinyl]-1H-benzimidazole (LansoprazoleN-Oxide)

213476-12-1 100mgN

+

OF

F F

O

S

N H

N

O

MM0474.08 Lansoprazole Sulphone N-Oxide 953787-54-7 100mgN

+

OF

F F

O

S

N H

N

O O

Levodropropizine

MM1246.05 Levodropropizine N-Oxide 152237-40-6 100mgN

+O

OH

OH

N

Levomepromazine Maleate

MM0019.11 Levomepromazine Sulfone N-Oxide (Levomepromazine N,S,S-Trioxide) n/a 50mg

O

N+

ON

SOO

Lidocaine Hydrochloride

MM0102.01Imp. B (EP): 2-(Diethylazinoyl)-N-(2,6-dimethylphenyl)acetamide (Lidocaine N2-Oxide)

2903-45-9 100mgO

NH

N+

O

Linezolid

MM3300.04 Linezolid N-Oxide 189038-36-6 100mgN

+

O

O

F N

O

NH

O

O

Loperamide Hydrochloride

MM0025.09 Imp. F (EP): Loperamide Oxide 106900-12-3 100mgN

+

O

Cl

OH

N

O

Loratadine

MM0257.21 Loratadine N-Oxide 165739-62-8 100mgN

O

O

N+O

Cl




MM0257.22 Loratadine Epoxide N-Oxide 1432057-93-6 100mgN

O

OO

N+O

Cl

Loxapine Succinate

MM1530.04 Loxapine N-Oxide 25967-34-4 100mg N

N+ O

N

O

Cl

Mebhydrolin Napadisilate

MM1891.01 Mebhydrolin N-Oxide 210408-26-7 100mgN

N+

O

Mebrofenin

MM3594.01 Mebrofenin N-Oxide n/a 50mgBr

NH

N+

OHO

O

OH

O

O

Meclozine Hydrochloride

MM0586.05 Meclozine N-Oxide 114624-69-0 10mgCl

N

N+

O

Melperone

MM0321.01 Melperone N-Oxide n/a 100mgO

N+

O

F

Mepacrine Hydrochloride

MM1695.02 Mepacrine N-Oxide Dihydrochloride n/a 100mg 2HCl

NH

N+

O

O

N

Cl

Mepivacaine Hydrochloride

MM0368.06 Mepivacaine N-Oxide n/a 100mg NH

N+

OO

Mepyramine Maleate

MM0559.05 Mepyramine N-Oxide Dihydrochloride n/a 100mg2

HCl

NN

+ O

NO




Mequitazine

MM3131.01 Mequitazine N-Oxide n/a 100mg H

N+ O

N

S

AND Enantiomer

Methapyrilene Hydrochloride

MM1680.01 Methapyrilene N-Oxide 78761-79-2 100mgN

+N

S

N

O

Methenamine

MM1998.01 Methenamine N-Oxide 62190-92-5 100mgN

N+

NN

O

Metoclopramide

MM0073.07Imp. G (EP): N'-(4-Amino-5-chloro-2-methoxybenzoyl)-N,N-diethylethane-1,2-diamine N-Oxide(Metoclopramide N-Oxide)

171367-22-9 100mg NH

N+

O

O

ONH 2

Cl

Mianserin Hydrochloride

MM0147.06 Mianserin N-Oxide 62510-46-7 100mgN

+

N

O

Mifepristone

MM1007.02 Mifepristone N-Oxide 91934-98-4 100mgO

H

H

OHN

+O

Mirtazapine

MM1005.02Imp. A (EP): (14bRS)-2-Methyl-1,2,3,4,10-14b-hexahydropyrazino[2,1-a]pyrido[2,3-c][2]benzazepine 2-Oxide

155172-12-6 100mg N

N

N+

O

Moclobemide

MM0250.03 Moclobemide N-Oxide 64544-24-7 100mgO

Cl

NH

N+

O

O




Morphine Hydrochloride

MM0037.03Imp. F (EP): (17S)-7,8-Didehydro-4,5 -epoxy-17-methylmorphinan-3,6 -diol17-Oxide (Morphine N-Oxide)

639-46-3 CS 100mg H

N+O

OH O HO

Morphine Sulphate

MM0037.03Imp. F (EP): (17S)-7,8-Didehydro-4,5 -epoxy-17-methylmorphinan-3,6 -diol 17-Oxide(Morphine N-Oxide)

639-46-3 CS 100mg H

N+O

OH O HO

Mycophenolate Mofetil

MM1001.07Imp. G (EP): 2-(Morpholin-4-yl)ethyl (4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoate N-Oxide

224052-51-1 100mgOH

ON

+

O

O

OO

O

O

Nalbuphine Hydrochloride

MM0341.02 Nalbuphine N-Oxide Hydrochloride n/a 100mgN

+O

OOH O H

OH HCl

Naloxone Hydrochloride Dihydrate

MM0272.03 Naloxone N-Oxide 112242-14-5 100mgN

+O

OH

OH OO

Nefazodone Hydrochloride

MM0591.02 Nefazodone N-Oxide n/a 100mg N

NN

N+

N Cl

O

O

O

Nevirapine Anhydrous

MM1146.06 Nevirapine N10-Oxide 1027324-99-7 50mg

O

N+

N N

NH

O

MM1146.07 Nevirapine N1-Oxide 162255-73-4 100mgNH

N N+

O

N

O

Nicardipine Hydrochloride

MM0465.04 Nicardipine N-Oxide n/a 100mgNH

O

O

ON

+

OO

N+

O

O




Nicotine

MM0517.07 Imp. E (EP): (1RS,2S)-1-Methyl-2-(pyridin-3-yl)pyrrolidine 1-Oxide (Nicotine N -Oxide) 491-26-9 100mg N

+

O

N

MM0517.08 3-[(1S,2S)-1-Methyl-1-oxidopyrrolidin-2-yl]pyridine (Nicotine cis-N'-Oxide) 51095-86-4 50mg N N

+

O

MM0517.19 (1RS,2S)-Nicotine N,N'-Dioxide (3-[(1RS,2S)-1-Methyl-1-oxidopyrrolidin-2-yl]pyridine 1-Oxide) 2055-29-0 100mg N

+ON

+

O

&1

Mixed

Nikethamide

MM0627.02 Nikethamide N-Oxide Hydrochloride n/a 100mg HClN+

N

O

O

Ofloxacin

MM0228.10Imp. F (EP) as Hydrochloride: 4-[(RS)-6-Carboxy-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-10-yl]-1-methylpiperazine 1-Oxide Hydrochloride (Ofloxacin N-Oxide Hydrochloride)

n/a 100mg HCl

O

N

O

OH

O

F

N

N+

O

Olanzapine

MM0329.03Imp. D (EP): 1-Methyl-4-(2-methyl-10H-thieno-[2,3-b][1,5]benzodiazepin-4-yl)piperazin-1-oxide(Olanzapine N-Oxide)

174794-02-6 50mgN

N+O

N

NH

S

Olopatadine Hydrochloride

MM1261.09(Z)-3-[2-(Carboxymethyl)dibenzo[b,e]oxepin-11(6H)-ylidene]-N,N-dimethylpropan-1-amine Oxide Hydrochloride (OlopatadineN-Oxide Hydrochloride)

n/a 100mgHCl

O

OH

N+

O

O

Omeprazole

MM0095.07Imp. E (EP): 4-Methoxy-2-[[(RS)-(5-methoxy-1H-benzimidazol-2-yl)sulphinyl]methyl]-3,5-dimethylpyridine 1-Oxide (Omeprazole N-Oxide)

176219-04-8 100mgN

+

O

O

S

O

N H

N

O

MM0095.16Imp. I (EP): 4-Methoxy-2-[[(5-methoxy-1H-benzimidazol-2-yl)sulphonyl]methyl]-3,5-dimethylpyridine 1-Oxide(Omeprazole Sulphone N-Oxide)

158812-85-2 100mgN

+

O

O

S

N H

N

O

O O

Opipramol Dihydrochloride

MM0422.03 Opipramol N-Oxide n/a 100mg N N

N+

OHO

MM0422.08 Opipramol Di-N-Oxide n/a 50mg N N+

N+

OHO

O




Oxatomide

MM1115.01 Oxatomide N-Oxide n/a 100mg N

N+

NN H

OO

Oxeladin Hydrogen Citrate

MM0547.01 Oxeladin N-Oxide n/a 10mg OO

N+

O

O

Oxomemazine

MM0958.04 Oxomemazine N-Oxide Hydrochloride(Trimeprazine Sulphone N-Oxide Hydrochloride) n/a 100mg HCl

N N+

OSO

O

Oxybuprocaine Hydrochloride

MM0543.05 Oxybuprocaine N-Oxide Dihydrochloride n/a 100mg 2HCl

ON

+

O

O

O

NH2

Oxycodone Hydrochloride

MM0672.06 Oxycodone N-Oxide 71539-52-1 50mg

N+O

O

OH

OO

Pantoprazole Sodium Sesquihydrate

MM0099.06 Pantoprazole N-Oxide 953787-60-5 100mgN

+

O

O

O

S

N H

N

O

FF

O

MM0099.07 Pantoprazole Sulphone N-Oxide 953787-55-8 100mgN

+

O

O

O

S

N H

N

O

FF

O O

Perphenazine

MM0826.03 Perphenazine N1-Oxide 803615-00-1 100mg S

N N

N+

OHO

Cl

MM0826.05 Perphenazine Sulfoxide N1-Oxide (Perphenazine N1,S-Dioxide) n/a 100mg S

N N

N+

OHO

Cl

O

MM0826.08 Perphenazine Sulfoxide N1,N4-Dioxide (PerphenazineN1,N4,S-Trioxide) n/a 100mg

OS

Cl

N N+

O

N+

OOH

MM0826.09 Perphenazine N1,N4-Dioxide Monohydrochloride n/a 100mg HClS

N N+

N+

OHO

O

Cl

MM0826.10 Perphenazine Sulfoxide N1,N4-Dioxide Dihydrochloride(Perphenazine N1,N4,S-Trioxide Dihydrochloride) n/a 100mg 2

HCl

Cl

N N+

N+

OOH

O

SO

MM0826.11 Perphenazine Sulfone N1,N4-Dioxide Dihydrochloride(Perphenazine N1,N4,S,S-Tetraoxide Dihydrochloride) n/a 100mg 2

HCl

OSO

Cl

N N+

O

N+

OOH




Pheniramine Maleate

MM0059.04 Pheniramine N-Oxide 12656-98-3 100mg

N

N+ O

Pioglitazone Hydrochloride

MM0616.09 Pioglitazone N-Oxide 145350-09-0 100mg N+

O

N HS

O

O

O

Pramoxine Hydrochloride

MM3228.01 Pramoxine N-Oxide n/a 100mg N+

O

O

O

O

Pridinol Hydrochloride

MM3493.02 Pridinol N-Oxide n/a 100mgN

+

OOH

Pridinol Mesilate

MM3493.02 Pridinol N-Oxide n/a 100mgN

+

OOH

Procainamide Hydrochloride

MM0550.02 Procainamide N-Oxide Dihydrochloride n/a 100mg2

HClNH

N+O

O

NH2

Procaine Hydrochloride

MM0596.02 Procaine N-Oxide 1027072-50-9 100mg ON

+ O

NH 2

O

Prochlorperazine Maleate

MM0411.13 Prochlorperazine Sulfone N1,N4-Dioxide Dihydrochloride(Prochlorperazine N1,N4,S,S-Tetraoxide Dihydrochloride) n/a 50mg 2

HCl

Cl

N N+

O

N+

O

SO

O

Procyclidine Hydrochloride

MM1573.01 Procyclidine N-Oxide n/a 100mgN

+O

OH

Promethazine Hydrochloride

MM0412.05 Promethazine Sulphoxide N-OxideHydrochloride 1135334-50-7 100mg HCl

N

SO

N+ O




Protopine

MM2571.01 Protopine N-Oxide 87264-51-5 100mgO

O

N+

O

O

O

O

Proxymetacaine Hydrochloride

MM0404.02 Proxymetacaine N-Oxide Dihydrochloride n/a 50mg2

HClON

+

O

O

O

NH 2

Quetiapine Fumarate

MM1130.10 Imp. H (EP): 2-[2-[4-(Dibenzo[b,f][1,4]thiazepin-11-yl)-1-oxidopiperazin-1-yl]ethoxy]ethanol (Quetiapine N-Oxide) 1076199-40-0 50mg N

N+ O

OH

O

N

S

Quinine Dihydrochloride

MM0458.01 Quinine N-Oxide 109906-48-1 100mgOH

N+

O

HH

N

O

MM0458.05 Quinine N,N'-Dioxide (Quinine Di-N-Oxide) 101655-92-9 50mgOH

N+

O

HH

N+

O

O

Quinine Hydrochloride

MM0458.01 Quinine N-Oxide 109906-48-1 100mgOH

N+

O

HH

N

O

Rabeprazole Sodium

MM0618.04Imp D (EP): 2-[[(RS)-(1H-Benzimidazol-2-yl)sulfinyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-Oxide (Rabeprazole N-Oxide)

924663-38-7 100mg SNH

N

O

N+

O

O

O

MM0618.05

Imp I (EP): 2-[[(1H-Benzimidazol-2-yl)sulfonyl]methyl]-4-(3-methoxypropoxy)-3-methylpyridine 1-Oxide (RabeprazoleSulphone N-Oxide)

924663-37-6 100mg SNH

N

OO

N+

O

O

O

Raloxifene Hydrochloride

MM0738.01Imp. C (EP): [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-[2-(piperidin-1-yl)ethoxy]-phenyl]methanone N-Oxide (Raloxifene N-Oxide)

195454-31-0 50mgO

N+

O

O

S

OH

OH

Ranitidine Hydrochloride

MM0086.05Imp. E (EP): N-[2-[[[5-[(Dimethyloxidoamino)-methyl]furan-2-yl]methyl]sulphanyl]ethyl]-N'-methyl-2-nitroethene-1,1-diamine (RanitidineN-Oxide)

73857-20-2 100mgO

N+

OS

NH

NH

N+

O

O




Reserpine

MM1423.01 Reserpine N-Oxide 474-48-6 100mgN

+ ONH H

H

O

O

O

O

O

O

O

O

H

O

Rifabutin

MM0633.06 Rifabutin N-Oxide 645406-37-7 100mgO

O

OOOHO

NH

OH

OO

O

OH

N+O

NHN

Rifampicin

MM0514.05 Imp. B (EP) as Hydrochloride: Rifampicin N-OxideHydrochloride n/a 100mg

OH

OH

O

OO

OH

NH

O OH OO

O

OH

NN

N+

O

HCl

Risperidone

MM0491.21 Risperidone cis-N-Oxide n/a 100mg N

O

N+

O F

N O

N

MM0491.22 Risperidone trans-N-Oxide n/a 50mg N

O

N+

O F

N O

N

Rizatriptan Benzoate

MM1313.08 Imp. H (EP): N,N-Dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine N-Oxide (Rizatriptan N-Oxide) 260435-42-5 100mg

NH

N+O

N

N

N

Roflumilast

MM3618.05 Roflumilast N-Oxide 292135-78-5 50mg NH

N +

Cl

OClO

O

F F

O

Ropinirole Hydrochloride

MM0331.10 Ropinirole N-Oxide Hydrochloride n/a 100mg HCl

NH

O

N+

O

Rotigotine Hydrochloride

MM1403.10 Rotigotine N-Oxide Hydrochloride n/a 50mg N+

O

OH

SHCl

Sildenafil Citrate

MM0254.04Imp. B (EP): 5-[2-Ethoxy-5-[(4-methyl-4-oxidopiperazin-1-yl)sulfonyl]phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Sildenafil N-Oxide)

1094598-75-0 100mg SN

N+O

OO

O

N

NH

O

NN




Strychnine Nitrate

MM0658.02 Strychnine N-Oxide Hydrochloride 139369-62-3 100mgN

+O

O

H

H

H

O

N

HCl

Sulforidazine

MM1195.04 Sulforidazine 5-Sulfone N-Oxide (Sulforidazine N,S5,S5-Trioxide) 53926-90-2 100mg

N+

ON

S

SO O

OO

Sulpiride

MM0051.06Imp. F (EP): 1-Ethyl-2-[[(2-methoxy-5-sulphamoylbenzoyl)amino]methyl]pyrrolidine1-Oxide (Sulpiride N-Oxide)

n/a 100mg N+

NH

O

SO

ON H 2 O

O

Sumatriptan Succinate

MM0310.04Imp. D (EP) as Maleate: N,N-Dimethyl-2-[5-[(methylsulfamoyl)methyl]-1H-indol-3-yl]-ethanamine N-Oxide Maleate

n/a 100mgO

OH

O

OHSNH

O ONH

N+

O

Tamoxifen Citrate

MM0053.18 Tamoxifen N-Oxide 75504-34-6 100mgO

N+

O

Terbinafine Hydrochloride

MM0696.12 Terbinafine N-Oxide Hydrochloride n/a 100mg HCl

ON

+

Terconazole

MM1286.03 Terconazole N-Oxide n/a 100mg N+O

O

ClCl

N

N

N

OON

AND Enantiomer

MM1286.04 Terconazole Di-N-oxide Dihydrochloride n/a 100mg N+O

N+

O ON

N

N

Cl Cl

OO

2HCl

AND Enantiomer

Tetracaine Hydrochloride

MM0504.02 Tetracaine N-Oxide 55750-02-2 100mg ON

+ OO

NH

Thebaine

MM0244.01 Thebaine N-Oxide 81600-02-4 100mg

OO O

N+O




Thioridazine Hydrochloride

MM0116.07 Thioridazine N-Oxide 103827-30-1 50mg N+

ON

S

S

Ticlopidine Hydrochloride

MM0150.16 Ticlopidine N-Oxide 79923-55-0 100mg N+

S

ClO

Tramadol Hydrochloride

MM0007.11 Tramadol N-Oxide 147441-56-3 100mgN +

O

OOH

AND Enantiomer

Trazodone Hydrochloride

MM0421.13

Imp. A (BP) as Hydrochloride: 4-(3-Chloro-phenyl)-1-[3-(3-oxo-2,3-dihydro-1,2,4-triazolo[4,3-a]pyridin-2-yl)propyl]piperazineN1-Oxide Hydrochloride (Trazodone N-OxideHydrochloride)

55290-66-9 50mg HClClN

N+

N

NN

O O

Trifluoperazine Hydrochloride

MM0441.07 Trifluoperazine Sulfoxide N1,N4-Dioxide (TrifluoperazineN1,N4,S-Trioxide) 150111-58-3 100mg

FF

F

N N+

O

N+

O

SO

MM0441.08 Trifluoperazine N4-Oxide Dihydrochloride n/a 100mg 2HCl

FF

F

N N

N+

O

S

MM0441.09 Trifluoperazine Sulfone N1,N4-Dioxide (TrifluoperazineN1,N4,S,S-Tetraoxide) n/a 100mg

FF

F

N N+

O

N+

O

SO

O

MM0441.11 Trifluoperazine N1,N4-Dioxide 150111-57-2 100mgFF

F

N N+

O

N+

O

S

MM0441.12 Trifluoperazine N1-Oxide 52172-24-4 100mg S

N N+

N

O

F

F F

Triflupromazine Hydrochloride

MM1675.04 Triflupromazine Sulfoxide N-Oxide (Triflupromazine N,S-Dioxide) 94163-91-4 100mg

FF

F

N N+

OSO

MM1675.08 Triflupromazine N-Oxide Hydrochloride n/a 100mg HClS

N N+

O

F

F F




MM1675.09 Triflupromazine Sulfone N-Oxide Hydrochloride(Triflupromazine N,S,S-Trioxide Hydrochloride) n/a 100mg HClSO

O

N N+

O

F

F F

Trihexyphenidyl Hydrochloride

MM0237.04 Trihexyphenidyl N-Oxide 161564-79-0 50mgN

+OOH

Trimebutine

MM0417.17 Trimebutine N-Oxide Hydrochloride n/a 100mgO

O

ON

+O

O

OHCl

Trimeprazine Tartrate

MM0958.04 Trimeprazine Sulphone N-Oxide Hydrochloride(Oxomemazine N-Oxide Hydrochloride) n/a 100mg HCl

N N+

OSO

O

MM0958.07 Trimeprazine Sulfoxide N-Oxide (Trimeprazine N,S-Dioxide) n/a 100mg N N+

OSO

MM0958.08 Trimeprazine N-Oxide Hydrochloride n/a 100mg HClS

N N+

O

Trimetazidine Dihydrochloride

MM0539.13 Trimetazidine N-Oxide Dihydrochloride n/a 100mg 2HCl

O

O

O

N+

NH

O

Trimethobenzamide Hydrochloride

MM3281.02 Trimethobenzamide N-Oxide n/a 100mg ON

+ON

H

O

O

O

O

Trimipramine Maleate

MM0240.04Imp. A (EP): (2RS)-3-(10,11-Dihydro-5H-dibenzo-[b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-amineN-oxide (Trimipramine N-Oxide)

14171-70-1 100mg N+

NO

Tripelennamine Hydrochloride

MM1631.01 Tripelennamine N-Oxide 60317-19-3 100mgN

NN

+O

Tropicamide

MM0601.05 Tropicamide N-Oxide n/a 100mgN

+

O

N

OH

O




Vardenafil Hydrochloride Trihydrate

MM1569.03 Vardenafil N-Oxide 448184-48-3 100mg NN

O

NH

NS

OO

N

N+

OO

Venlafaxine Hydrochloride

MM0393.14 Venlafaxine N-Oxide 1094598-37-4 100mg N+ O

OH

O

Vincamine

MM0519.02 Vincamine N-Oxide 51442-60-5 100mgN

+ OH

OH

OO

N

Vinpocetine

MM0406.06 Vinpocetine N-Oxide 109741-24-4 100mg

O

O

H

NN

+

O

Xanthinol Nicotinate

MM1048.01 Xanthinol N-Oxide n/a 100mgN

O

N

N+

OH

O

OH

NNO

Zolmitriptan

MM0298.05 Zolmitriptan N-Oxide 251451-30-6 100mg

O

ON H

N+

O

NH

Zopiclone

MM0149.01Imp. A (EP): (5RS)-6-(5-Chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-Methylpiperazine-1-carboxylate 4-Oxide(Zopiclone Oxide)

43200-96-0 100mg N

Cl

N

ON

N

O

O

N

N+

O


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Whilst every effort has been made to ensure the accuracy of the information in this catalogue, customers are directed to their local sales office or theLGC Standards website for further details and to verify product information. Specifications, terms and pricing are subject to change. LGC does notguarantee availability and reserves the right to discontinue any product. LGC does not accept liability for any loss that is caused by inaccurate productinformation, customer selection or inappropriate use of a product. Unless otherwise stated all trademarks are the property of LGC or its affiliated groupcompanies. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying,recording or any retrieval system, without the written permission of the copyright holder. © LGC Limited, 2017. All rights reserved. STD/0031/SL/0717.

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